Tobacco product



United States Patent 3,381,690 TOBACCO PRODUCT Joseph N. Schumacher, Winston-Salem, N.C., assignor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Nov. 8, 1965, Ser. No. 506,861 9 Claims. (Cl. 131-17) This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobacco smoke.

It is well known in the tobacco art that the flavor and aroma of the tobacco product and the smoke from the tobacco are very important considerations insofar as the ultimate consumer is concerned. Considerable efforts are exerted by the manufacturers of tobacco products to provide a product that will be acceptable to the consumer, particularly as regards flavor and aroma characteristics. It has been the common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide smoking tobacco which has a pleasing flavor and aroma before and during smoking. However, such a procedure is costly and may at times become prohibitive in the event that certain types of tobacco may be in short supply. Accordingly, it is a further object of this invention to provide a new class of additive materials which when applied to the tobacco products improve and enhance the flavor and aroma of these products and the smoke emitted therefrom, thereby increasing or enhancing the pleasure and other values that may be derived by the consumer from the use of these products.

A further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.

An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.

A still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.

Further and additional objects will appear from the following description and the appended claims.

In accordance with one embodiment of this invention, a tobacco product is provided to which has been added or which has been treated with a small amount of a compound selected from the group of compounds having the formula:

t t CH; (it-R 0 Formula I wherein R is hydrogen or methyl. When R is hydrogen the tobacco additive is S-methylfurfuraldehyde and when R is methyl the compound is -methyl-2-acetyl-funan.

The following specific examples illustrate the preparation and characteristics of the tobacco additives of the present invention. It will be appreciated, however, that this invention is not limited to the specific processes by which the compounds may be prepared. All temperatures are expressed in degrees centigrade.

Example II.Synthesis and properties of S-methylacetyl-furan This compound was synthesized, according to the procedure of N. I. Shuikin and I. F. Belskii, J. Gen. Chem. (U.S.S.R.) 29, 10664068 (1959), from 41 grams of methylfur-an, 76.5 grams of acetic anhydride, and 3 milliliters of phosphoric acid. This gave 17 grams of S-methyl- Z-acetyl-furan, boiling point 75-76/9 millimeters; nuclear magnetic resonance spectrum; 1-=7.68(3); 758(3); 3.82-(1) and 2.84(1).

Example II.Synthesis and properties of 5-methylfurfuraldehyde This compound was synthesized according to the procedure of V. J. Traynelis, J. J. Miskel, In, and I. R. Sowa, J. Org. Chem., 22, 1269-70 (1957), from 26 grams of dimethylformamide, 54 grams of phosphorous oxychloride and 25 grams of 2-methylfuran. This gave 25 grams of S-methylfurfuraldehyde, boiling point 70/11 millimeters; nuclear magnetic resonance spectrum: =7.52 (3);3.68(1);2.74(1);and0.37.

It has been found that the tobacco additives of the invention when incorporated into tobacco products impart a flavor and aroma both before and during smoking which many smokers consider to be desirable in smoking products. However, it is pointed out that the methods for defining or characterizing the quality of a flavor or aroma in the tobacco art are almost purely subjective and different smokers may define the same flavor quite differently. The tobacco additive of Example I imparts an aromatic, spicy aroma and imparts a-strong tobacco-like taste to tobacco smoke. The tobacco additive of Example II imparts an aroma and flavor which some characterize as similar to bitter almonds.

In accordance with this invention, a compound embraced by generic Formula I or mixtures thereof is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.001 to 2.0 percent by weight of the product. Preferably the amount of additive is between about 0.01 and 1.0 percent by weight in order to provide a tobacco product having a desired flavor and aroma. However, the amount used will depend upon the amount of flavor and aroma desired and the particular compound or mixture thereof that is used. The additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes or other smoking articles are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.

In accordance with one specific embodiment of this invention, an aged, flue-cured and shredded tobacco is sprayed with a 1% ethyl alcohol solution of 5-methyl-2- acetyl-furan in an amount to provide a tobacco containing 0.1 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor.

The additives falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive. Thus water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other flavorand aroma-producing additives, such as those disclosed in US. Patents Nos. 2,766,145, 2,905,575, 2,905,576, 2,- 978,365 and 3,041,211 may be incorporated into the tobacco with the additive of this invention.

While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco,

cigars or other tobacco products. Furthermore, the compounds may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.

Also, the invention has been particularly described with reference to the addition of the compounds directly to tobacco. However, it will be apparent that the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also it may be incorporated into the filter tip, the packaging material or the seam paste employed for gluing the cigarette paper. Thus, a tobacco product is provided which includes the specified additives and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.

While several particular embodiments of this invention are shown above, it will be understood, of course, that the invention is not to be limited thereto, since many modifications may be made, and it is contemplated, therefore, by the appended claims, to cover any such modifications as fall within the true spirit and scope of this invention.

I claim:

1. A tobacco product having added thereto an amount sufiicient to alter the flavor or aroma of a tobacco product of a compound selected from the group consisting of S-methylfurfuraldehyde and 5-methyl-2-acetyl-furan.

2. The product recited in claim 1 wherein the amount of flavorant is between about 0.001 and 2.0 percent by weight of the product.

3. The product recited in claim 1 wherein the amount of flavorant is between about 0.01 and 1.0 percent by Weight of the product.

4. A tobacco product having added thereto and dispersed therein a small amount sufficient to improve the flavor thereof of S-methylfurfuraldehyde.

5. The product recited in claim 4 wherein the amount of fiavorant is between about 0.001 and 2.0 percent by weight of the product. 1

6. The product recited in claim 4 wherein the amount of fiavorant is between about 0.01 and 1.0 percent by weight of the product.

7. A tobacco product having added thereto a small amount sufiicient to improve the flavor thereof of S-methyl-Z-acetyl-furan.

8. The product recited in claim 7 wherein the amount of flavorant is between about 0.001 and 2.0 percent by weight of the product.

9. The product recited in claim 7 wherein the amount of flavorant is between about 0.01 and 1.0 percent by weight of the product.

References Cited UNITED STATES PATENTS 3,082,125 3/1963 Bavley et al. 131-17 3,280,824 10/1966 Roberts 99140 X SAMUEL KOREN, Primary Examiner.

D. I. DONOHUE, Assistant Examiner. 

1. A TOBACCO PRODUCT HAVING ADDED THERETO AN AMOUNT SUFFICIENT TO ALTER THE FLAVOR OR AROMA OF A TOBACCO PRODUCT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF 5-METHYLFURFURALDEHYDE AND 5-METHYL-2-ACETYL-FURAN. 